The Best Way to Gamble on the Tourney

Tuesday night I was standing on the top floor of a sports bar in Chicago, cash in hand, heart rate up, bidding on college basketball teams like they were livestock at a county fair.

It was the 21st NCAA Tournament “Calcutta” auction I’ve organized, and it’s my favorite way to gamble on big field events.

The pot landed in the high five-figures, teams were flying off the board, and by the end of the night I’d invested enough to buy a used car.

I’ll tell you all about it below, including what a Calcutta is if this is your first time hearing the term.

I’ll also highlight a Juice Reel competition I intend to win, and share some opening round tournament bets for our Bets of the Week!

Let’s get after it.

The “Calcutta” Auction

A Calcutta is a live auction pool tied to a large-field sporting event.

It works for anything with a bracket or a leaderboard: March Madness, the Masters, the World Cup.

A group gathers, a field of competitors gets auctioned off one by one, and every dollar bid goes into a collective pot. If you win a team (or a golfer, or a country), you own their result. You can buy 1 team or 20 teams, up to you.

Advance far enough, you get paid. Lose early, you eat the cost. It combines the social energy of a live auction with the stakes of tiered futures betting, and it rewards both sports knowledge and auction discipline.

My Version

I’ve been running a March Madness Calcutta in Chicago for more than 20 years. This year was the 21st annual edition, held Tuesday night at a rented-out venue with a professional auctioneer calling the lots.

All 68 tournament teams are covered across 52 lots: seeds 1 through 12 in each region sell individually, First Four play-in opponents are bundled as a single lot, and seeds 13 through 16 in each region are packaged together.

The payout structure is what keeps everyone engaged.

Every team that reaches the Sweet Sixteen earns money for its owner, and the payouts escalate sharply from there.

There are also bonus payouts for the biggest blowout losses in Rounds 1 and 2 (so even a 30-point loss can pay), plus a payout for the highest individual single-game scorer.

My Strategy

Some people walk into a Calcutta with a short list of teams they want and bid emotionally when those names come up. I do the opposite.

Before the auction I model the fair value of every lot based on each team’s probability of reaching each payout threshold.

On auction night, I’ll buy anyone I believe is priced below fair value and pass on anyone who isn’t, regardless of how much I like them as a basketball team. Some years that means I walk out with 12 teams. This year it was eight.

I invested 19.7% of the total pot. Here’s the portfolio:

The portfolio is top-heavy by design. Duke and Illinois account for nearly 14% of the pot between them. They’re my Final Four contenders.

If Duke wins the championship (24% payout), that single team covers my entire investment with room to spare. If Duke reaches the Final Four and two of my other teams sneak into the Sweet Sixteen, I’m roughly at breakeven.

The cheaper lots (Ohio State, High Point, SMU, the Hawaii bundle) are lottery tickets. They cost almost nothing, but a surprise Sweet Sixteen run at 0.2% of the pot returns 2%, which is a 10x payout.

The Price Tags

The most expensive lot at our event was Arizona at 10.2% of the pot. That’s at the high end of the historical range for a 1 seed. Duke and Michigan both went for 8.8%, and Florida sold at 6.6%. The room clearly believed in the top seeds this year, which makes sense given how top-heavy this field is.

On the other end, High Point and McNeese both went for the least (0.2% of the pot). Not a lot of faith in the mid-majors!

Run Your Own

If you’ve never done a Calcutta with your group, I can’t recommend it enough. It’s an electric way to bet the tourney!

The event itself has good drama, and the group chat is on fire for all game days. If you’re in the Chicago area and want an invite to next year’s auction, reply to this email and I’ll consider adding you to the list!

Follow My Pursuit of the Reel National Championship

I’m competing in Juice Reel’s “REEL National Champ” betting contest this year as the #8 seed of 64 bettors.

I’m pacing well against my (so far absent) first round opponent today, as I’m up $700+ today and he hasn’t placed a bet.

If you want to root me on or bet with me, follow my profile (InsiderOB) on Juice Reel. I’ll be posting updates as the rounds progress – hope to be in the Sweet 16 by next newsletter.

Bet(s) of the Week

Last week we took an L in this section. Texas A&M’s money line didn’t come through, costing us one half unit.

We were profitable again in the “Values I Like” futures section from last week, with St. John’s winning the Big East Tournament at +200, but I don’t track those in the official running total.

Back to the official tally: since starting the newsletter, bets in this section are ahead 23.36 units, with a +15.5% ROI.

A $100 bettor would be up $2,336 if they tailed every bet. We’ll keep tallying weekly.

Based on my research, I am making the following bets this week:

BYU Money Line @ -132 on BallyBet for 0.5 units (Today, 7:25 PM ET)

BYU is not perfect, but Texas is more flawed. The Longhorns’ no-help, isolation-forcing defense sounds daunting until you realize BYU has AJ Dybantsa (25.3 PPG, potential #1 pick) and Rob Wright, two of the best on-ball creators. When BYU faced Utah’s similar drop/no-help scheme, Dybantsa and Wright combined for 64 points.

Texas’ lone true big, Matas Vokietaitis, fouled out in 26 minutes against NC State on Tuesday. BYU’s relentless downhill attack should get to the line early and often, tilting this game in their favor.

UNI +10 @ -110 on Fanatics for 0.5 units (Friday, 7:10 PM ET)

UNI is a top-25 defense on both KenPom and Torvik, and their pack line scheme walls off the rim (9th percentile rim rate allowed) while allowing the lowest transition rate in the country, shutting down exactly how St. John’s likes to score.

Since getting healthy in early February, the Panthers rank 44th in adjusted efficiency and won four games in four days as a 6 seed to take the MVC tournament.

Jordan Majewski at Basket Under Review flagged UNI as his biggest potential upset in the East Region, and ten points is a lot of cushion for a team built to grind.